I’m prepared for criticism, but please let me ask for serious relationship advice.

I’m genuinely struggling. Sorry for asking yet another question. I’m a woman in my 20s with Dating Type C. I don’t know how to date. I have no experience with romantic relationships with men. I had my first experience at 17 with a man in his 50s whom I met through a dating site, for several hundred thousand yen. Since then, I’ve spent the past seven years focused solely on papa-katsu (compensated dating in Japan), maintaining relationships as a kept woman. I’ve never once dated anyone I could call a boyfriend. I automatically view men in terms of what I stand to gain or lose, and I don’t understand what it means to genuinely like someone. Even so, there is one man with whom I’ve maintained a strange, dinner-friend-like relationship for about two years. He’s 15 years older than me, divorced, and we met through university-related activities. He has nothing to do with this kind of world. He pursued me very intensely two years ago, but at the time, I saw “older men” as people who gave me money. Since there was no money involved, I decided the relationship wasn’t worth pursuing and cut off contact for nearly a year and nine months. Around February this year, I suddenly decided to reach out to him. He replied right away, and since then we’ve gone out for dinner about seven times. However, nothing has progressed, and we’re still just in a relationship where we eat dinner together (sob). We meet at 6 p.m., eat until 8, he puts me in a taxi home, and we say goodbye. That’s what we repeat every time. I think we both know that we like each other and could start dating if things continue this way. He also often says and does things that seem to indicate he’s interested, but since he hasn’t confessed his feelings or made any direct moves when we meet, we’ve ended up being nothing more than dinner companions. The things he’s said that make me think he’s interested include: ・“You seem different somehow! You’ve become even prettier!” ・“I don’t think there’s any man who could turn you down if you asked him out.” ・When I told him over LINE that I liked him, he replied, “I like you too.” ・“The age gap is so big that I feel guilty, as though I were dating my daughter.” ・“If I had the opportunity, I’d like to get married again.” On the way home in the taxi, we always hold hands and chat. Even though we’ve known each other for nearly two years, we still haven’t even kissed. Recently, before we part, he’s also started saying, “I’d like to spend more time together next time.” I reply, “Yes, I’d like to spend more time together too.” I take “spend more time together” to mean staying overnight, but we always finish after just two hours of dinner—and he eats incredibly quickly, so it somehow feels rather rushed instead of relaxed. I suspect he’s more shy than you might expect and doesn’t have the courage to confess his feelings first. That said, I don’t believe he’s only looking for something casual or treating me carelessly or lightly. Should I encourage him to confess his feelings and suggest staying over myself? If so, how should I invite him? Until now, my only experience has been physical relationships with married men, dating clubs, and working as a hostess, so I don’t know how to move a real romantic relationship forward. Normally, I could just go along with the flow—have a conversation focused on the man, which wasn’t particularly interesting (sorry), and then go to a hotel. But ordinary romance has all these steps and feels difficult. Also, compared with how much I’ve earned in the past, I have very little savings, and I haven’t been able to hold down a job for very long. I know it’s my own fault, but I feel hopeless about my life. Part of me can’t take the next step because I feel guilty, wondering whether someone like me is really allowed to have a normal relationship with a decent man. What do you think this man is thinking, and how should I move this relationship forward? Or should I be more bold and approach it the way I would with men from a dating club? I’m sorry for the long post. To those of you with more life experience, could you please give me some advice? I’m asking despite being prepared for criticism, so please don’t let this get deleted…